US3451833A - Organosilicon binders - Google Patents

Organosilicon binders Download PDF

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US3451833A
US3451833A US491897A US3451833DA US3451833A US 3451833 A US3451833 A US 3451833A US 491897 A US491897 A US 491897A US 3451833D A US3451833D A US 3451833DA US 3451833 A US3451833 A US 3451833A
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siloxanate
binders
compounds
parts
ethylcalcium
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US491897A
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Eckhard Bonitz
August Rettig
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BASF SE
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BASF SE
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    • E—FIXED CONSTRUCTIONS
    • E04—BUILDING
    • E04C—STRUCTURAL ELEMENTS; BUILDING MATERIALS
    • E04C2/00—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels
    • E04C2/02—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials
    • E04C2/04—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials of concrete or other stone-like material; of asbestos cement; of cement and other mineral fibres
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
    • C04B26/30—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Other silicon-containing organic compounds; Boron-organic compounds
    • C04B26/32—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Other silicon-containing organic compounds; Boron-organic compounds containing silicon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups

Definitions

  • Organosilicon binders comprising (a) orgauosilanol, polycondensation product or reaction product thereof and '(b) organometallic silanolate or organometallic siloxanate.
  • organosilicon binders are obtained by mixing organosilanols or their polycondensation products or reaction products with organometal silanolates or organometall siloxanates.
  • Organosilanols include particularly monoorganosilanetriols, i.e. compounds containing three hydroxyl groups for each silicon atom.
  • Polycondensation products and reaction products include for example monoorganosiloxanols or other products which contain SiOH-, Si-H-, SiNH, Si-O-C- or SiSi groups in an arrangement of the atoms in a chain, and not only on terminal members of the chain, but also at least on some, and in some cases on all, other members of the chain.
  • These include dimers and trimers of diorganosilanediols containing Si-0H or Si--OR groups as terminal groups, R denoting an alkyl group.
  • These compounds may be represented for example by the following formulae:
  • CH1 C2H5 CgHs n 2, 3, 4 about 1000 e.g. n and m in the molar ratio 1:1
  • the compounds are in general liquid and may be used as such or in solution. It is obviously also possible to use the compounds in solid form by converting them into the solid form for example by adsorption on conventional adsorbents, for example silica gel, cork powder, polystyrene foam flakes, wood chips, pumice granulate, polyurethane foam, cellulose, paper or aluminum oxide.
  • Organometallic silanolates or organometallic siloxanates include in particular the appropriate calcium compounds.
  • the compounds may exclusively or partly contain other metals, for example aluminum, magnesium, titanium, zirconium, iron, chromium, nickel, cobalt, tin and lead.
  • Such compounds may be represented for example by the following formulae in which R denotes an alkyl, aryl or alkenyl radical:
  • reaction products are known. They may be prepared from silanes by adding on olefins followed by treatment with water or from organosilicon chloride compounds with water.
  • Organocalcium silanolates and organocalcium siloxanates may be prepared from organochlorosilanes and calcium hydroxide or from organosilanols or organoalkoxysilanes and calcium oxide. Corresponding compounds of other metals are formed using other metal oxides or metal hydroxides.
  • the binders according to this invention can also contain fillers. These includes both active fillers, for example cement which actively reacts in the setting of the binder, and also passive fillers, for example finely divided polystyrene foam, which during setting are merely passively enclosed.
  • active fillers for example cement which actively reacts in the setting of the binder
  • passive fillers for example finely divided polystyrene foam, which during setting are merely passively enclosed.
  • fillers examples include: sand, slate powder, alumina, rock such as limestone, marble, granite, basalt, quartz, dolomite, silica, silicates, metal oxides, such as A1203, F6 Ti02, PbO2, CI'203, Z110, SiOz, metal hydroxides, such as Al(OH) Mg(OH) Fe(OH) diatomite, vermiculite, mica, asbestos, inorganic glasses, particularly silicate glasses, glass wool, slag wool, ceramic materials, such as porcelain, stoneware, fireclay, brick, cement of all types, gypsum, phosphate, polyphosphoric acids, cellulose, cellulosic materials, such as wood, straw, paper, cork, peat, reeds, cellulose esters, cellulose ethers and also polycondensation products, such as polyesters, polyamides, and polycarbonates and phenoplast or aminoplast resins.
  • metal hydroxides such as Al(OH) Mg(OH) Fe(OH
  • Plastics particularly polymers of c p-unsaturated organic polymerisable compounds, for example of olefins, such as ethylene, propylene, isobutylene, styrene, a-methylstyrene or vinyltoluenes, and of 1,3-dienes, such as butadiene or isoprene, are also suitable.
  • olefins such as ethylene, propylene, isobutylene
  • styrene a-methylstyrene or vinyltoluenes
  • 1,3-dienes such as butadiene or isoprene
  • Polymers of vinyl chloride or vinylidene chloride or of esters of acrylic or methacrylic acid with alcohols having one to eight carbon atoms may also be used.
  • Styrene homopolymers and styrene copolymers have a particular importance among the said compounds.
  • the organic plastics may be in the form of powder, granulate in the form of beads, flakes, chips, small tubes, small rods, plates or fibres.
  • Finely divided expanded plastics for example ethylene or styrene foam polymers, have special importance as fillers because the binders according to this invention are particularly suitable for bonding organic materials to inorganic materials.
  • Group A are organosilanols and Organosiloxanes
  • group B are the calcium siloxanates
  • group C are the fillers.
  • Setting occurs when at least one substance of group A is brought into contact with at least one substance from group B.
  • Organosiloxanates of divalent metals or of metals of higher valency give higher mechanical strengths after cure than the corresponding compounds of metals which merely form monovalent ions. If the acid components, particularly silicic acid components, of the organosilicon binders according to this invention are neutralized by metal oxides, the cured materials are distinguished by unusual resistance both to acids and bases or water. Whereas for example ethylpolysiloxane resin is readily dissolved by solutions of caustic soda in methanol at room temperature, a cured ethylpolysiloxane resin having an appropriate content of ethylcalcium siloxanate is substantially resistant to alcoholic caustic alkali solutions.
  • the setting process is substantially a condensation in which the increase in the size of the molecule takes 4 place, depending on the type of substances, by elimination of water, alcohols, hydrogen gas or even ammonia.
  • Example 1 a binder mixture is described which contains the following components:
  • Parts A 100 B 50 C 2000 The following is the usual procedure:
  • Components B and C are mixed dry. Liquid component A is sprayed onto the resultant mixture. If desired a certain amount of water (for example 10% by weight of H 0) may be added to the solution A prior to spraying. The water may however be sprayed into the mixture last of all or it may be omitted if it is desired that the mixture should set slowly, the moulding or coating then being moistened subsequently.
  • a certain amount of water for example 10% by weight of H 0
  • Another application of the process according to this invention for example for the production of mouldings resembling artificial stone, consists in mixing B and C together, adding A, shaping the mixture and treating the moulding with steam. Steam treatment achieves high strengths in a short time. Mixtures having a higher proportion of filler still give good mechanical properties when cured with steam.
  • the binders may be used for making artifical stone, for bonding stone to stone, for making plasticised and elasticised mixtures of lime, mortar or cement-mortar, for coating artificial and natural stone with plastics, such as polyolefins, polystyrene, polybutadiene and rubber, for making shaped articles of wood, peat, straw, reeds, cellulose and other cellulosic materials, if desired with sand and cement. They may be used as joint adhesives.
  • They may also be used for: bonding artificial stone to wood, bonding wood to wood, bonding wood to plastics, bonding metal to plastics, bonding metal to stone, bonding metal to wood, bonding leather and bonding ceramics.
  • Example 1 Parts Ethylsiloxane (formula given above) (A) 1000 Ethylcalcium siloxanate (formula given above) (B) 500 Quartz sand C(a) 7500 Portland cement 275. C(b) 2500 II Ethylisiloxane 1000 Ethylcalcium siloxanate 200 Quartz sand 9700 Portland cement 275 100 ExampleZ I Ethylphenylsiloxane 1000 CIHB Ca a HO S:iO S iO H (A) L011 1. LEE .1.
  • Ethylcalcium siloxanate (B) Calcium 'metasilicate (Ca) 100 Pumice granulate (Cb) 7500 II A 100 B 100 Ca 100 Cb 10,000 Example 10 Parts Ethylsiloxane (A) 1000 Ethylcalcium siloxanate 1000 Referring to the examples:
  • Mixtures set out under I are suitable for use for example as joint adhesives or coating agents.
  • Mixtures set out under II and III may serve for the production of mouldings.
  • the liquid requirement for mixtures II is about 500 parts of the mixture of water and alcohol for each 1000 parts of A. In this way a cure time is achieved which allows about twenty hours before mouldings are strong enough to be transported.
  • the vinylsiloxane binder in Example 3 is an exception, for it sets in about forty minutes, and the methylsiloxane binder in Example 9, which sets in about fifteen minutes, is another exception.
  • Alcohol and water are interchangeable. An excess of alcohol causes slower setting, while an excess of water causes more rapid setting.
  • Mixture I in Example 3 may be used as a primer for concrete surfaces, for example to render layers of unsaturated polyester resin adherent thereto.
  • MixtureI in Example 4 gives chipboard having great resistance to water when press molded in a pre ss at 100 C. at a pressure of about 50 atmospheres gauge.
  • Mixtupre I in Example 5 may be used for filling cavities, for example for thermal insulation.
  • Mixture I in Example 6 may be used for making floorcoverings.
  • Example 7 The mixtures in Example 7 are binders or molding materials reinforced by asbestos fibres.
  • Example 8 The mixtures in Example 8 are binders containing cork, and in Example 9 binders containing pumice. Both are distinguished by very low water adsorption.
  • An organosilicon binder comprising: (a) a member selected from the group consisting of lower alkyl silanols, lower alkenyl silanols, alkylene disilanols, phenyl silanols and siloxanes thereof and (b) a member selected from the group consisting of solid or semi-sold calcium silanolate and solid or semi-sold calcium siloxanate.
  • component (b) is calcium siloxanate.
  • a binder as claimed in claim 1 which also contains a filler.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Ceramic Engineering (AREA)
  • Materials Engineering (AREA)
  • Civil Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)

Description

United States Patent US. Cl. 106-287 4 Claims ABSTRACT OF THE DISCLOSURE Organosilicon binders comprising (a) orgauosilanol, polycondensation product or reaction product thereof and '(b) organometallic silanolate or organometallic siloxanate.
We have found that valuable organosilicon binders are obtained by mixing organosilanols or their polycondensation products or reaction products with organometal silanolates or organometall siloxanates.
Organosilanols include particularly monoorganosilanetriols, i.e. compounds containing three hydroxyl groups for each silicon atom. Polycondensation products and reaction products include for example monoorganosiloxanols or other products which contain SiOH-, Si-H-, SiNH, Si-O-C- or SiSi groups in an arrangement of the atoms in a chain, and not only on terminal members of the chain, but also at least on some, and in some cases on all, other members of the chain. These include dimers and trimers of diorganosilanediols containing Si-0H or Si--OR groups as terminal groups, R denoting an alkyl group. These compounds may be represented for example by the following formulae:
CH1 C2H5 CgHs n=2, 3, 4 about 1000 e.g. n and m in the molar ratio 1:1
Aktiengesellschaft, Ludwigs- 5 3,451,833 Patented June 24, 1969 ice n=40 mole m=60 mole ag. n= mole m=20 mole e.g. n=95 mole 1n=5 mole The compounds are in general liquid and may be used as such or in solution. It is obviously also possible to use the compounds in solid form by converting them into the solid form for example by adsorption on conventional adsorbents, for example silica gel, cork powder, polystyrene foam flakes, wood chips, pumice granulate, polyurethane foam, cellulose, paper or aluminum oxide.
Organometallic silanolates or organometallic siloxanates include in particular the appropriate calcium compounds. Instead of calcium, the compounds may exclusively or partly contain other metals, for example aluminum, magnesium, titanium, zirconium, iron, chromium, nickel, cobalt, tin and lead. Such compounds may be represented for example by the following formulae in which R denotes an alkyl, aryl or alkenyl radical:
a J Lu, *H
e.g. n= mole m=10 mole and reaction products are known. They may be prepared from silanes by adding on olefins followed by treatment with water or from organosilicon chloride compounds with water.
Organocalcium silanolates and organocalcium siloxanates may be prepared from organochlorosilanes and calcium hydroxide or from organosilanols or organoalkoxysilanes and calcium oxide. Corresponding compounds of other metals are formed using other metal oxides or metal hydroxides.
The binders according to this invention can also contain fillers. These includes both active fillers, for example cement which actively reacts in the setting of the binder, and also passive fillers, for example finely divided polystyrene foam, which during setting are merely passively enclosed.
Examples of such fillers are: sand, slate powder, alumina, rock such as limestone, marble, granite, basalt, quartz, dolomite, silica, silicates, metal oxides, such as A1203, F6 Ti02, PbO2, CI'203, Z110, SiOz, metal hydroxides, such as Al(OH) Mg(OH) Fe(OH) diatomite, vermiculite, mica, asbestos, inorganic glasses, particularly silicate glasses, glass wool, slag wool, ceramic materials, such as porcelain, stoneware, fireclay, brick, cement of all types, gypsum, phosphate, polyphosphoric acids, cellulose, cellulosic materials, such as wood, straw, paper, cork, peat, reeds, cellulose esters, cellulose ethers and also polycondensation products, such as polyesters, polyamides, and polycarbonates and phenoplast or aminoplast resins.
Plastics, particularly polymers of c p-unsaturated organic polymerisable compounds, for example of olefins, such as ethylene, propylene, isobutylene, styrene, a-methylstyrene or vinyltoluenes, and of 1,3-dienes, such as butadiene or isoprene, are also suitable. Polymers of vinyl chloride or vinylidene chloride or of esters of acrylic or methacrylic acid with alcohols having one to eight carbon atoms may also be used. Styrene homopolymers and styrene copolymers have a particular importance among the said compounds.
The organic plastics may be in the form of powder, granulate in the form of beads, flakes, chips, small tubes, small rods, plates or fibres.
Finely divided expanded plastics, for example ethylene or styrene foam polymers, have special importance as fillers because the binders according to this invention are particularly suitable for bonding organic materials to inorganic materials.
The components of the binders are hereinafter included in groups. Group A are organosilanols and Organosiloxanes, group B are the calcium siloxanates and group C are the fillers.
With regard to the setting and use of the binders in practice, the following may be said:
Setting occurs when at least one substance of group A is brought into contact with at least one substance from group B.
Organosiloxanates of divalent metals or of metals of higher valency give higher mechanical strengths after cure than the corresponding compounds of metals which merely form monovalent ions. If the acid components, particularly silicic acid components, of the organosilicon binders according to this invention are neutralized by metal oxides, the cured materials are distinguished by unusual resistance both to acids and bases or water. Whereas for example ethylpolysiloxane resin is readily dissolved by solutions of caustic soda in methanol at room temperature, a cured ethylpolysiloxane resin having an appropriate content of ethylcalcium siloxanate is substantially resistant to alcoholic caustic alkali solutions.
The setting process is substantially a condensation in which the increase in the size of the molecule takes 4 place, depending on the type of substances, by elimination of water, alcohols, hydrogen gas or even ammonia.
We have found that alcohols have a regulating effect on the setting process.
In Example 1 below, a binder mixture is described which contains the following components:
A.Ethylsiloxane as a liquid component (50% by weight solution in propanol) having the approximate composition:
n w HOS1OH Parts A 1000 B C 1000 For the preparation of a moulding resembling artificial stone, the following are mixed together:
Parts A 100 B 50 C 2000 The following is the usual procedure:
Components B and C are mixed dry. Liquid component A is sprayed onto the resultant mixture. If desired a certain amount of water (for example 10% by weight of H 0) may be added to the solution A prior to spraying. The water may however be sprayed into the mixture last of all or it may be omitted if it is desired that the mixture should set slowly, the moulding or coating then being moistened subsequently.
Another application of the process according to this invention, for example for the production of mouldings resembling artificial stone, consists in mixing B and C together, adding A, shaping the mixture and treating the moulding with steam. Steam treatment achieves high strengths in a short time. Mixtures having a higher proportion of filler still give good mechanical properties when cured with steam.
The binders may be used for making artifical stone, for bonding stone to stone, for making plasticised and elasticised mixtures of lime, mortar or cement-mortar, for coating artificial and natural stone with plastics, such as polyolefins, polystyrene, polybutadiene and rubber, for making shaped articles of wood, peat, straw, reeds, cellulose and other cellulosic materials, if desired with sand and cement. They may be used as joint adhesives.
They may also be used for: bonding artificial stone to wood, bonding wood to wood, bonding wood to plastics, bonding metal to plastics, bonding metal to stone, bonding metal to wood, bonding leather and bonding ceramics.
The following list gives examples of binders according to this invention:
Example 1 Parts Ethylsiloxane (formula given above) (A) 1000 Ethylcalcium siloxanate (formula given above) (B) 500 Quartz sand C(a) 7500 Portland cement 275. C(b) 2500 II Ethylisiloxane 1000 Ethylcalcium siloxanate 200 Quartz sand 9700 Portland cement 275 100 ExampleZ I Ethylphenylsiloxane 1000 CIHB Ca a HO S:iO S iO H (A) L011 1. LEE .1. (12:90 mole%; m= mole%) Ethylcalcium siloxanate (B) 500 Quartz sand (0.2 to 0.5 mm particle size) (Ca) 7500 Portland cement 275. (Cb) 2500 Ethyl-phenylsiloxane (A) 1000 Ethylcalciumsiloxanate (B) 200 Quartz sand (0.2 to 0.5 mm. particle size) Ca) 9700 Portland cement 275. (Cb) 100 Examp1e3 I Vinyllsiloxane 1000 CH=CHFI HO--S|i0 H(n20) (A) OH in Ethylcalcium siloxanate (B) 150 Quartz sand (0.2 to 1 mm. particle size) (C) 1500 II Vinylsiloxane 1000 Ethylcalcium siloxanate 500 Quartz sand (0.2 to 1 mm.) 10,000 III Vinylsiloxane 1000 Ethylcalcium siloxanate 200 Quartz sand (0.2 to 1 mm.) 9800 Example 4 I Propylsiloxane 100 I (131171 Ho'-sl-o H n20(A) LQH ..ln
'Propylcalcium siloxanate (B) 20 Wood chips. (C) 1500 II Parts Propylsiloxane (A) 1000 Propylcalcium siloxanate (B) 500 Wood chips. (C) 10,000
III Propylsiloxane 1000 Propylcalcium siloxanate 200 Wood chips 9800 ExampleS I Propylsiloxane (A) 150 Propylcalcium siloxanate (B) 20 Polystyrene foam flakes. (C) 1200 II Propylsiloxane 1000 Propylcalcium siloxanate 500 Polystyrene foam flakes 10,000 HI Propyl siloxane 1000 Propylcalcium siloxanate 200 Parts Polystyrene foam flakes 9800 Example6 Polycondensate of diphenylsilanediol and methyl silicate (A) 150 Methylcalcium siloxanate (B) 20 Polypropylene flakes (C) 2000 II A 1000 B 500 C 10 ,000 III A 1000 B 200 C 9800 Example7 Polycondensate of diethylsilanediol and ethyl silicate (A) 500 Ethylcalcium siloxanate (B) Asbestos fibres (Ca) 4000 Portland cement 375 (Ob) 500 II A 1000 B 200 Ca 9700 Cb 100 Example 8 Ethylsiloxane dissolved in ethyltriethyoxysilane (A) 100 Methylcalcium siloxanate (B) 20 Cork granulate (C) 1500 Parts A 1000 B 200 C 9800 Example9 I Methylsiloxane (A) 1000 CH u 1 HO -S|10-H (n50) L H J1:
Ethylcalcium siloxanate (B) Calcium 'metasilicate (Ca) 100 Pumice granulate (Cb) 7500 II A 100 B 100 Ca 100 Cb 10,000 Example 10 Parts Ethylsiloxane (A) 1000 Ethylcalcium siloxanate 1000 Referring to the examples:
Mixtures set out under I are suitable for use for example as joint adhesives or coating agents.
Mixtures set out under II and III may serve for the production of mouldings.
For stirring mixtures I, about 600 parts of alcohol (mixture of equal parts of C to C and about 200 parts of water are added to each 1000 parts of A.
The liquid requirement for mixtures II is about 500 parts of the mixture of water and alcohol for each 1000 parts of A. In this way a cure time is achieved which allows about twenty hours before mouldings are strong enough to be transported.
The vinylsiloxane binder in Example 3 is an exception, for it sets in about forty minutes, and the methylsiloxane binder in Example 9, which sets in about fifteen minutes, is another exception.
Alcohol and water are interchangeable. An excess of alcohol causes slower setting, while an excess of water causes more rapid setting.
Mixture I in Example 3 may be used as a primer for concrete surfaces, for example to render layers of unsaturated polyester resin adherent thereto.
The same mixture gives coatings resembling enamel on metal surfaces, such as iron or stainless steel.
MixtureI in Example 4 gives chipboard having great resistance to water when press molded in a pre ss at 100 C. at a pressure of about 50 atmospheres gauge.
Mixtupre I in Example 5 may be used for filling cavities, for example for thermal insulation.
Mixture I in Example 6 may be used for making floorcoverings.
The mixtures in Example 7 are binders or molding materials reinforced by asbestos fibres.
The mixtures in Example 8 are binders containing cork, and in Example 9 binders containing pumice. Both are distinguished by very low water adsorption.
We claim:
1. An organosilicon binder comprising: (a) a member selected from the group consisting of lower alkyl silanols, lower alkenyl silanols, alkylene disilanols, phenyl silanols and siloxanes thereof and (b) a member selected from the group consisting of solid or semi-sold calcium silanolate and solid or semi-sold calcium siloxanate.
2. A binder as claimed in claim 1 in which component (b) is calcium siloxanate.
3. A binder as claimed in claim 1 which also contains a filler.
4. A binder as claimed in claim 3 in which the filler is cement.
References Cited UNITED STATES PATENTS 3,061,587 10/1962 Rust.
3,098,050 7/1963 Noll.
3,153,000 10/1964 Takimoto.
3,152,999 10/ 1964 Rust.
3,190,762 6/1965 Carlson.
2,813,085 11/1957 MacMullen.
FOREIGN PATENTS 746,038 3/ 1956 Great Britain.
MORRIS LIEBMAN, Primary Examiner.
L. T. JACOBS, Assistant Examiner.
US. Cl. X.R. 260-37, 825
US491897A 1964-10-14 1965-09-30 Organosilicon binders Expired - Lifetime US3451833A (en)

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DEB78909A DE1239850B (en) 1964-10-14 1964-10-14 Process for the production of organosilicon binders

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4960835A (en) * 1984-02-27 1990-10-02 Raychem Limited Preparation of organic polymers using organometallic terminated blocks to produce metal free block copolymers
EP0566936A1 (en) * 1992-04-09 1993-10-27 Dow Corning Toray Silicone Company, Limited Aquatic antifouling mortar composition
WO1995011751A1 (en) * 1993-10-26 1995-05-04 E. Heller & Company Photocatalyst-binder compositions
US5616532A (en) * 1990-12-14 1997-04-01 E. Heller & Company Photocatalyst-binder compositions
US5849200A (en) * 1993-10-26 1998-12-15 E. Heller & Company Photocatalyst-binder compositions
US5939194A (en) * 1996-12-09 1999-08-17 Toto Ltd. Photocatalytically hydrophilifying and hydrophobifying material
US6013372A (en) * 1995-03-20 2000-01-11 Toto, Ltd. Method for photocatalytically rendering a surface of a substrate superhydrophilic, a substrate with superhydrophilic photocatalytic surface, and method of making thereof
US6090489A (en) * 1995-12-22 2000-07-18 Toto, Ltd. Method for photocatalytically hydrophilifying surface and composite material with photocatalytically hydrophilifiable surface
US6165256A (en) * 1996-07-19 2000-12-26 Toto Ltd. Photocatalytically hydrophilifiable coating composition
US6337129B1 (en) 1997-06-02 2002-01-08 Toto Ltd. Antifouling member and antifouling coating composition
US6399678B2 (en) * 1998-06-25 2002-06-04 Tamko Roofing Products Silicone-aggregate mixtures for pumping and spraying applications
US6830785B1 (en) 1995-03-20 2004-12-14 Toto Ltd. Method for photocatalytically rendering a surface of a substrate superhydrophilic, a substrate with a superhydrophilic photocatalytic surface, and method of making thereof
US20070282060A1 (en) * 2006-06-06 2007-12-06 Wacker Chemie Ag Crosslinkable Compositions Based On Organosilicon Compounds
EP2942375A1 (en) 2014-05-05 2015-11-11 Rolvaplast Textured PVC panel

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CH684946A5 (en) * 1993-03-30 1995-02-15 Warmoctro Bv Putty.

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US2813085A (en) * 1954-01-27 1957-11-12 Cowles Chem Co Aqueous cementitious composition containing an alkali metal silanol salt
US3098050A (en) * 1957-11-08 1963-07-16 Bayer Ag Building material compositions for the manufacture of water repellent masonry
US3061587A (en) * 1960-05-03 1962-10-30 Hughes Aircraft Co Ordered organo silicon-aluminum oxide copolymers and the process of making same
US3152999A (en) * 1960-05-31 1964-10-13 Hughes Aircraft Co Stable organo siloxy-aluminum oxide polymers and process of producing same
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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4960835A (en) * 1984-02-27 1990-10-02 Raychem Limited Preparation of organic polymers using organometallic terminated blocks to produce metal free block copolymers
US5616532A (en) * 1990-12-14 1997-04-01 E. Heller & Company Photocatalyst-binder compositions
EP0566936A1 (en) * 1992-04-09 1993-10-27 Dow Corning Toray Silicone Company, Limited Aquatic antifouling mortar composition
WO1995011751A1 (en) * 1993-10-26 1995-05-04 E. Heller & Company Photocatalyst-binder compositions
US5849200A (en) * 1993-10-26 1998-12-15 E. Heller & Company Photocatalyst-binder compositions
US5854169A (en) * 1993-10-26 1998-12-29 E. Heller & Company Photocatalyst-binder compositions
US6093676A (en) * 1993-10-26 2000-07-25 E. Heller & Company Photocatalyst-binder compositions
US6830785B1 (en) 1995-03-20 2004-12-14 Toto Ltd. Method for photocatalytically rendering a surface of a substrate superhydrophilic, a substrate with a superhydrophilic photocatalytic surface, and method of making thereof
US6013372A (en) * 1995-03-20 2000-01-11 Toto, Ltd. Method for photocatalytically rendering a surface of a substrate superhydrophilic, a substrate with superhydrophilic photocatalytic surface, and method of making thereof
US6090489A (en) * 1995-12-22 2000-07-18 Toto, Ltd. Method for photocatalytically hydrophilifying surface and composite material with photocatalytically hydrophilifiable surface
US6524664B1 (en) 1996-03-21 2003-02-25 Toto Ltd. Photocatalytically hydrophilifying and hydrophobifying material
US6165256A (en) * 1996-07-19 2000-12-26 Toto Ltd. Photocatalytically hydrophilifiable coating composition
US5939194A (en) * 1996-12-09 1999-08-17 Toto Ltd. Photocatalytically hydrophilifying and hydrophobifying material
US6337129B1 (en) 1997-06-02 2002-01-08 Toto Ltd. Antifouling member and antifouling coating composition
US6399678B2 (en) * 1998-06-25 2002-06-04 Tamko Roofing Products Silicone-aggregate mixtures for pumping and spraying applications
US20070282060A1 (en) * 2006-06-06 2007-12-06 Wacker Chemie Ag Crosslinkable Compositions Based On Organosilicon Compounds
EP1865029A2 (en) * 2006-06-06 2007-12-12 Wacker Chemie AG Crosslinkable compositions based on organosilicon compounds
EP1865029A3 (en) * 2006-06-06 2008-11-19 Wacker Chemie AG Crosslinkable compositions based on organosilicon compounds
US7745531B2 (en) 2006-06-06 2010-06-29 Wacker Chemie Ag Crosslinkable compositions based on organosilicon compounds
EP2942375A1 (en) 2014-05-05 2015-11-11 Rolvaplast Textured PVC panel

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DE1239850B (en) 1967-05-03
GB1115783A (en) 1968-05-29
FR1449462A (en) 1965-08-12

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